3-Aminobenzyl alcohol → HCID 58467880, compound

HRID 1614941Notes

Reaction equation

HRID 1614941 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH3:10])[C:5]([Cl:19])=[CH:4][N:3]=1.[NH2:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH2:24][OH:25].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>O1CCOCC1>[Cl:19][C:5]1[C:6]([NH:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH3:10])=[N:7][C:2]([NH:20][C:21]2[CH:22]=[C:23]([CH2:24][OH:25])[CH:26]=[CH:27][CH:28]=2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 802933-Aminobenzyl alcoholHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 58467862HCID 58467862, compound

Product 1

HCID 58467880HCID 58467880, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

Into a reaction flask were added 2,5-dichloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]pyrimidin-4-amine (0.21 g, 0.70 mmol), 1,4-dioxane (20 mL), 3-aminobenzyl alcohol (0.13 g, 1.0 mmol), and p-toluenesulfonic acid monohydrate (0.049 g, 0.26 mmol). The mixture was heated at 105° C. for 2 days. To the reaction mixture was added NaHCO3 (saturated aqueous solution) and the organic solvent was removed under vacuum. Water and EtOAc were added to the residue. The aqueous layer was extracted with EtOAc twice. The organic layers were combined, dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column chromatography to give the desired product (0.27 g, 96%). LCMS for C20H22ClN4O2 (M+H)+: m/z=385.1.

Workup

  1. customthe organic solvent was removed under vacuum
  2. additionWater and EtOAc were added to the residue
  3. extractionThe aqueous layer was extracted with EtOAc twice
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-cb7c6edead6640adbec59f81e811fd5c
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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